452972-07-5Relevant articles and documents
Regioselective Amination or Alkoxylation of Halogenated Amino-, Thio- or Alkoxypyridines via Pyridyne Intermediates
Djukanovic, Dimitrije,Heinz, Benjamin,Idriess, Mohamed,Knochel, Paul,Martin, Benjamin,Siemens, Fiona
, (2021/11/26)
The treatment of 3-halopyridines (Cl, Br) bearing an R-substituent in position 2 (R = OEt, NEt2, N-piperidyl, or SEt) or in position 5 (R = OMe, OEt, SEt, NMe2, NEt2, or aryl) with KHMDS and an amine at 25 C for 12 hours in THF provided regioselectively 3
Triarylbismuthanes as threefold aryl-transfer reagents in regioselective cross-coupling reactions with bromopyridines and quinolines
Rao, Maddali L.N.,Dhanorkar, Ritesh J.
supporting information, p. 5214 - 5228 (2014/10/15)
Cross-coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd-catalysed conditions are disclosed. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one-pot strategy provided a simple and straightforward synthesis of both symmetrical and unsymmetrical diarylpyridines. Arylations of 2-bromo- and 3-bromoquinolines were achieved with triarylbismuth reagents. This study demonstrates that triarylbismuths may be used as threefold arylating reagents for the synthesis of aryl pyridines and quinolines through couplings with bromopyridines and bromoquinolines under Pd-catalysed conditions. Copyright
Fine-tuning the selectivity of aldosterone synthase inhibitors: Structure-activity and structure-selectivity insights from studies of heteroaryl substituted 1,2,5,6-tetrahydropyrrolo[3,2,1- ij ]quinolin-4-one derivatives
Lucas, Simon,Negri, Matthias,Heim, Ralf,Zimmer, Christina,Hartmann, Rolf W.
supporting information; experimental part, p. 2307 - 2319 (2011/06/20)
Pyridine substituted 3,4-dihydro-1H-quinolin-2-ones (e.g., 1-3) constitute a class of highly potent and selective inhibitors of aldosterone synthase (CYP11B2), a promising target for the treatment of hyperaldosteronism, congestive heart failure, and myocardial fibrosis. Among these, ethyl-substituted 3 possesses high selectivity against CYP1A2. Rigidification of 3 by incorporation of the ethyl group into a 5- or 6-membered ring affords compounds with a pyrroloquinolinone or pyridoquinolinone molecular scaffold (e.g., 4 and 5). It was found that these molecules are even more potent and selective CYP11B2 inhibitors than their corresponding open-chain analogues. Moreover, pyrroloquinolinone 4 exhibits no inhibition of the six most important hepatic CYP enzymes as well as a bioavailability in the range of the marketed drug fadrozole. The SAR studies disclose that subtle changes in the heterocyclic moiety are responsible for either a strong or a weak inhibition of the highly homologous 11-hydroxylase (CYP11B1). These results are not only important for fine-tuning the selectivity of CYP11B2 inhibitors but also for the development of selective CYP11B1 inhibitors that are of interest for the treatment of Cushing's syndrome and metabolic syndrome.
Pyrrolopyrimidines and Pyrrolopyridines
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Page/Page column 48, (2009/07/25)
Compounds of formula I in free or salt or solvate form, wherein X, T1, T3 and T4 have the meanings as indicated in the specification, are useful for treating diseases mediated by the ALK-5 and/or ALK-4 receptor. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.
Synthesis of 3,5-bis(2-indolyl)pyridine and 3-[(2-indolyl)-5-phenyl]pyridine derivatives as CDK inhibitors and cytotoxic agents
Jacquemard, Ulrich,Dias, Nathalie,Lansiaux, Amelie,Bailly, Christian,Loge, Cedric,Robert, Jean-Michel,Lozach, Olivier,Meijer, Laurent,Merour, Jean-Yves,Routier, Sylvain
, p. 4932 - 4953 (2008/12/21)
We here report the synthesis and biological evaluation of new 3,5-bis(2-indolyl)pyridine and 3-[(2-indolyl)-5-phenyl]pyridine designed as potential CDK inhibitors. Indole, 5-hydroxyindole, and phenol derivatives were used to generate three substitutions o
DIAZABICYCLIC COMPOUNDS USEFUL IN THE TREATMENT OF CNS AND OTHER DISORDERS
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Page 53-54, (2010/02/06)
The present invention relates to a compounds of formula (I): wherein A, B, D, E and F are defined herein; that are useful in treating central nervous system (CNS) diseases, disorders and conditions, such as but not limited to nicotine addiction, schizophr
Synthesis of novel halopyridinylboronic acids and esters. Part 2: 2,4, or 5-Halopyridin-3-yl-boronic acids and esters
Bouillon, Alexandre,Lancelot, Jean-Charles,Collot, Valerie,Bovy, Philippe R.,Rault, Sylvain
, p. 3323 - 3328 (2007/10/03)
This paper describes a general method for the synthesis and the isolation of novel 2,4, or 5-halopyridin-3-yl-boronic acids and esters 4, 7, 10, 13, 15. These compounds are prepared taking into account a regioselective halogen-metal exchange using nBuLi or a regioselective ortho-lithiation using lithium diisopropylamide and subsequent quenching with triisopropylborate starting from appropriate mono or dihalopyridines. All substrates studied to date provided a single regioisomeric boronic acid or ester product. Additionally, these compounds have been found to undergo Pb-catalyzed coupling with a range of arylhalides and authorize a strategy to produce new pyridines libraries.